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Rilmazafone & Avizafone

RedLeader

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तमसोमा ज्योतिर् गमया
Just read up on rilmazafone and avizafone, being prodrugs of the benzodiazopine variety. At first, it was in attempt to make a complete list of water-soluable (i.e. injectable) benzos, and through such I came across these.

Seeing as they are metabolized into active benzos once in the body, but don't cause any direct effect on benzo receptors (from Wiki on the former):

Rilmazafone has no effects on benzodiazepine receptors itself, but once inside the body is metabolised by aminopeptidase enzymes in the small intestine to form the active benzodiazepine 8-chloro-6-(2-chlorophenyl)-N,N-dimethyl-4H-1,2,4-triazolo [1,5-a] [1,4]benzodiazepine-2-carboxamide.
Source

I wonder how this would affect physical addiction. I cannot really seem to find any literature on this - how a benzodiazopine prodrug would contrast with more typical benzos when it comes to a tolerance and withdrawal symptoms. It's mainly curiosity, but has anybody ever looked into these drugs before, or prodrugs of the benzo variety in research? Or sampled?

I understand that fosazepam was engineered to be a (good) water-soluble derivative of diazepam, but why the need for a pro-diazepam as well? If it has nothing to do with dependency, why would such be administered as compared to alternatives?
 
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MurphyClox

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I wonder how this would affect physical addiction. I cannot really seem to find any literature on this - how a benzodiazopine prodrug would contrast with more typical benzos when it comes to a tolerance and withdrawal symptoms.
I would think that there are no major differences with regard to physical addiction. IIRC, the open-ring prodrug was developed mainly to overcome solubility problems of the classical closed-ring benzos.

After enzymatic ring closure (which happens quite early after uptake; partly in the intestines, partly in the liver) those compounds can be considered like the regular benzos.

- Murphy
 

Kae deNine

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does anyone know what the metabolites are for the Active metabolite of Rilmazafone???
as in, if taken, would you come up positive on 1) A dipstick benzo drug test, and 2) a gc/ms benzo drug test ...... meaning looking for all regular benzo metabolites I.E. diazepam, nordiaz, oxazepam, temazepam, clonazepam metabolites, etc....

any info would be appreciated. And yes, I've searched myself looking for info on this, and haven't been able to come to any definitive conclusions.

Also, the active metabolite of Rilmazafone is: 8-chloro-6-(2-chlorophenyl)-N,N-dimethyl-4H-1,2,4-triazolo [1,5-a][1,4]benzodiazepine-2-carboxamide.
As far as i know, it doesn't have a generic or shorter name.... please correct me if im wrong. But, as i hypothesize, I AM inclined to believe that this WOULD trip a benzo drug test seeing as it has as its skeleton, just like many of the popular mainstream benzo's, the 1,4-Benzodiazepine structure.

And again, please correct me if i am wrong in any of my assumptions or information. I am going on the best of my knowledge and gathered information. Thanks!
 

serotonin2A

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The desglycylated cyclic metabolite (8-chloro-6-(2-chlorophenyl)-N,N-dimethyl-4H-1,2,4-triazolo [1,5-a][1,4]benzodiazepine-2-carboxamide) is usually called M1. As far as I know no one has bothered to assign an INN (generic name) because it isn't an existing drug or an article of commerce. GC/MS could certainly be used to identify M1 and distinguish it from other benzodiazepines.

In terms of the metabolites of M1, here is what is known:

M4 - major metabolite in plasma and urine = 8-chloro-6-(2-chlorophenyl)-4H-1,2,4-triazolo [1,5-a][1,4]benzodiazepine-2-carboxylic acid
M3 - N,N-didesmethyl-M1 = 8-chloro-6-(o-chlorophenyl)-4H-1,2,4-triazolo-[1,5-a] [1,4] benzodiazepine-2-carboxamide
M2 - N-desmethyl-M1 = 8-chloro-6-(o-chlorophenyl)-N-methyl-4H-1,2,4-triazolo[1,5-a] [1,4] benzodiazepine-2-carboxamide
MA - 8-chloro-6-(o-chlorophenyl)-N-hydroxymethyl-4H-1,2,4-triazolo [1,5-a] [1,4]benzodiazepine-2-carboxamide
MD - 8-chloro-6-(o-chlorophenyl)-N-hydroxymethyl-N-methyl-4H-1,2,4-triazolo [1,5-a] [1,4]benzodiazepine-2-carboxamide

http://www.ncbi.nlm.nih.gov/pubmed/3428781
http://onlinelibrary.wiley.com/doi/10.1002/bdd.2510140402/pdf
http://www.ncbi.nlm.nih.gov/pubmed/3454653
http://www.ncbi.nlm.nih.gov/pubmed/2886322
 
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